A former teacher spent five years trying things that never quite fit. What finally worked was treating a new skill like a career change rather than a side project.
The turning point Holly Essington describes took place in an empty room of a beach house, in the middle of a family vacation, over Zoom. She had been offered her first placement as a remote appointment setter, and she stepped away from the holiday to accept it. “I remember feeling so accomplished and excited for the future,” she says.
She was 32, a mother of four, and five years out of the classroom.
The five years before
Essington left teaching in 2018 to stay home with her one-year-old son. She had already been tutoring online, and what followed became a sequence of experiments: in-person tutoring, blogging, social media management, a bakery run out of her house, network marketing.
“I knew I felt most like myself when I had a project or a job alongside motherhood,” she says. Each venture hit the same wall. The work kept expanding, and the time it consumed was the exact time she had left teaching to protect.
She also kept running into a framing that did not fit her. “Everywhere I looked, it felt like women were falling into one of two camps: the career woman or the homemaker. And I wanted a little bit of both.”
By late 2022, after a difficult fourth pregnancy and a move that left the family far from anyone they knew, she made a decision she still repeats to the women she trains: “This is the year I bet on myself and stop playing small.
The job nobody had explained to her
In early 2023 she came across remote appointment setting, a role she had never heard named despite years of looking for remote work.
The job sits inside the online education and services sector. A coach, course creator or agency promotes what they do, interested people arrive in the inbox, and someone has to talk to them: understand what they need, work out whether the programme is a sensible fit, and book the ones who are onto a call with a member of the sales team.
Essington is careful about what the role is not. No cold calling, no chasing, no selling to friends and family. She reaches for two analogies. The first is a barista, who does not have to convince anyone to want coffee because the customer already drove to the shop. The second is a luxury watch showroom, where the brand has done the work long before anyone walks through the door and the representative’s job is to handle the person who arrives.
What struck her was how much of the work drew on things she had already been doing for years without calling them professional skills.
“Empathy, active listening, reading a room, being the friend that people come to for advice,” she says. “These aren’t soft throwaway skills. These are the whole game.”
Teaching, she argues, is unusually good preparation. So is hospitality. So, in her telling, is talking a stubborn toddler into putting their shoes on.
Treating it like a career change
The shift she credits most is the one that sounds least exciting.
“I did not treat this opportunity as a hobby,” she says. “I approached it like I was going back to college for a career change.”
That belief now sits at the centre of what she teaches. Her argument runs as follows: businesses selling substantial programmes are not going to hand their inbox to someone who watched a cheap course over a weekend, any more than a hospital would hire someone who liked the idea of nursing. “Hiring without training or experience is hiring a liability, and a business wants assets.”
So the question she puts to prospective students is not whether the work exists, but whether they are prepared to train for it properly.
What Amplify Academy is
Essington founded Amplify Academy to build the training she says she wishes had existed when she started. The company reports having trained more than 500 women.
The programme is run entirely virtually, with no travel required. Cohorts are capped at 30 participants, a limit Essington says is deliberate, because every student’s practice conversations are reviewed by a coach rather than by software. The first phase covers the skill itself, after which students move into implementation, group coaching and one-to-one feedback on recorded role plays. Coaching continues after a student is placed with a company.
She is blunt about what the programme is not. It is not a shortcut, and she says so before anyone enrols.
“This is a real skill that takes energy and effort and time to build,” she says. “But once you have it, you can take it anywhere, and no one can take it from you.”
Her other recurring line is shorter: “Information is not power. Applied information is power.”
What she is actually arguing for
Underneath the training, Essington’s position is about who gets counted as skilled.
She spent five years being told, implicitly, that the useful version of her was either fully at work or fully at home. What she wanted was a profession that travelled with her, that did not require a personal brand, an audience or a business of her own, and that ran on abilities she already had.
“When you build your skill set, you set yourself free,” she says.
For a former teacher who once assumed the classroom was the only place her training counted, that is less a business pitch than a correction.
